He’s With Tom

He started out as a Patriots intern. Then Will McDonough made a very important friend, and got himself a much, much sweeter job.

Tom Brady appeared to the world in his underwear on April 16, 2005. The occasion was Saturday Night Live. A skit called for Brady to play a pants-less stud who charms ladies in the workplace. Even in briefs, Brady flashed some élan. For the reserved quarterback, it was a ballsy, half-naked bootleg into the New York limelight.

Already, Brady was dating a beautiful actress. Nestled among her boyfriend’s family, Bridget Moynahan beamed from the front row. Also watching were some of Brady’s closest friends on the Patriots, Dan Koppen and Larry Izzo. In their way, they had all helped lay the foundation for Brady’s burgeoning celebrity. And now, in his way, he was leaving them behind to crack into a new realm of stardom, a world that would soon offer up GQ covers, Visa endorsements, and Brazilian supermodels. Only one person in the audience that night would join Brady on this catapult ride to greater fame. His name was Will McDonough. He was an unexpected choice.

McDonough first pinged on the public radar three days after the SNL show, popping up in that fabulous junkyard of faux journalism, the Boston Herald’s Inside Track. He was described therein simply as “Tom’s bud.” In the years to come, as it grew apparent to hacks and flacks across town that Tom’s bud had been entrusted with a mysterious authority over Tom, McDonough became something more. He was Brady’s “assistant” or his “Man Friday.” When the gossipmongers were in a less generous mood, he was called a “butler” or a “pantry man.”

But McDonough’s role in Brady’s life has always been more substantial. For those who don’t remember, Brady was not all that long ago a floppy-haired underdog who favored blazers with elbow patches. Even after his early on-field success, he retained a dorky aw-shucks style. He hated the podium and was unprepared for celebrity. Then, before our eyes, he became the metrosexual who now flits about Europe, paparazzi in his wake. These days Brady seems quite comfortable in his underwear, accessorized perhaps with a sweaty bottle of Smartwater and some Stetson cologne. Compared with Peyton Manning, who hams it up for the NFL’s yeasty audience and wouldn’t be caught dead in a Movado watch, Brady is a fey extraterrestrial. He has leveraged his appeal in a restrained fashion that transcends his sport. The approach might even be called elegant. But the process has not been intuitive. Brady has needed help. That’s where McDonough comes in.

Although his duties are shrouded in secrecy, McDonough is a de facto manager; he brokers deals and acts as a gatekeeper. Brady seems to trust him implicitly. McDonough has had a major hand in the quarterback’s metamorphosis—and along the way has become an important man in his own right. One weekend, the Boston College grad might be hobnobbing with hedge fund managers. The next, he could be jetting to a celebrity-studded party. Always, he remains deeply connected to Brady as both a business associate and a best friend. Their relationship raises eyebrows, not least because of its clandestine nature. On the Patriots’ payroll until this past February, McDonough has now left the team to handle Brady’s affairs on his own. He has no official title. His business card simply lists his name, phone, and e-mail. It’s all so East Berlin.

Among both casual observers and Brady’s friends, the question comes up time and again: Just what in hell does Will McDonough do?

No one fully knows.

In the royal palace, intrigue dwells behind the throne. And in Brady’s kingdom, the courtly machinery is nearly impossible to observe. Access to the inner sanctum is granted only to longtime friends who have shown unwavering loyalty. This is where McDonough lives, shielded by an omerta he helps uphold. He is a puzzle inside a riddle, wrapped in Armani Exchange.

“I couldn’t pick him out of a lineup,” says Globe columnist Dan Shaughnessy.

“I know nothing about him,” says Shaughnessy’s colleague Bob Ryan. “He could be 5 feet 8, he could be 10 feet tall. He could be white, black. I don’t know.”

He is, in fact, a baby-faced 28-year-old from Westwood, soft around the edges, with a wisp of a Boston accent and an affinity for fine clothes and fancy cocktails. A fellow who in certain circles might be considered a dandy. (And who is no relation to the late Globe sportswriter who once punched out a surly Patriots cornerback in the locker room.) But the murkiness surrounding those details is, of course, by design. Not even those who claim to be “tight” with McDonough know much about him. McDonough himself refused to cooperate with this story, saying only, “A lot of people that I’ve known for my whole life don’t even know that I represent Tom. I don’t draw attention to myself. It’s not me.” (When this magazine tried to secure the rights to photos of him from Brady’s new website, we were told that only recent pictures could be used, as McDonough was working on his image and didn’t want anything unflattering to circulate. Then, within days, all of the photos of McDonough on the site were removed.)

Having the ear of Boston’s mightiest celebrity grants power. It also inspires dread. Of the several dozen people contacted for this story, only a handful would allow their names to be used. Even Don Yee, Brady’s longtime agent, quickly retreated under questioning, deferring to McDonough himself.

But what is it about McDonough’s role with Brady that requires such cloaking? He has been, at times, a bagman, a gofer, a buffer, a fixer, the scout who locks down a VIP table, the go-between who orchestrates Brady’s appearances. He gets tickets for Brady’s pals. He is both a consigliere and a 6-foot-tall human PDA whose contents you will never learn. Over the years, as McDonough has proven his worth, the responsibilities have expanded. He may once have looked something like the “butler” the Inside Track disparaged, but no longer. Almost anything in Brady’s life that doesn’t deal with football now gets funneled McDonough’s way. The idea is to have the quarterback focus on quarterbacking and keep both athlete and brand in fine fettle.

“His role is not of an assistant. He is a trusted confidant to Tom. He handles a sizeable portion of [Brady’s] private affairs,” says one of Brady’s closest friends, who responded to my questions through an intermediary. “That does not include ordering up long-stemmed roses or carrying the dog.”

Here’s a sampling of what it does include: McDonough has helped Brady find lawyers, modeling agents, and financial advisers. A licensed real estate agent, he’s been instrumental in developing the brownstone on Beacon Street where Brady sold the floors beneath his penthouse apartment. He liaises with the companies Brady endorses and is said to help hone their Brady-helmed advertising campaigns.

But McDonough’s input isn’t limited to business. While he may draw a paycheck from Brady, sources say the partnership is more brotherly than formal. He’s said to help Brady with almost anything—advice about girlfriends, family, which movie to see that weekend. In the inevitable Entourage analogy, McDonough falls “somewhere between an Eric and a Turtle,” according to another of Brady’s friends, though in truth he’s probably more like a hybrid of Eric and Ari. Yes, McDonough has cashed in on his friend’s stardom, but he also brings his own agentlike qualities to the table. He is by all accounts a savvy, hard-working, and discreet businessman. Friends say he’s charismatic, loyal, and down-to-earth, the kind of guy everyone wants to buy a drink for.

At the same time, just like Eric, McDonough has his detractors, those who see him as a lucky boob. A coattailer. And they aren’t afraid to voice their opinions, at least anonymously. On one blog, McDono
ugh is called an “ass clown,” a “jock sniffer,” a “douche,” and a “hog sucker.” Other people interviewed for this story expressed a disbelief bordering on outrage at his success. Invariably, though, the critics didn’t actually know him. They’d merely crossed his path at a party somewhere.

Perhaps McDonough elicits this prickly response because he’s managed to slip into a glittering palace we’ll never see the inside of. He’s not a stud athlete. He’s not an actor or a rock star or even a hot groupie. He comes off as a regular guy. To look at him is to wonder what’s so special; to think, Why not me?

How it is that McDonough got his foot in the door takes us back to 1996. At 16, most boys were playing Mortal Kombat. McDonough was hustling. He wanted to work at the sports radio station WEEI, and legend has it he called every day asking for a job. But McDonough’s former boss there, Lou Imbriano, has a different version of events: “His dad knew the CFO of our company.”

It was the beginning of a familiar pattern: McDonough leveraging a connection to advance himself, then quickly making a positive impact. “There was no sense of entitlement,” says Imbriano, now the head of TrinityOne marketing. “I’d ask him, ‘What are you doing on Saturday?’ and his answer was, ‘What do you need me to do?'”

Imbriano recounts one episode during the Patriots’ 1996 AFC championship game in Foxboro. McDonough was sent to the stadium parking lot, tasked with handing out large “Go Pats!” WEEI cards. But he was competing against the team’s marketing crew, which was handing out pompoms in the same spot. “More of the cards were coming into the stadium than the pompoms,” Imbriano says. “The next day I got a call giving me a little crap for it.”

During his senior year at Westwood High, where he was class president, McDonough started a staffing company to keep up with Imbriano’s demands for manpower at events. In short order, he had a sizable collection of classmates working for him. In 1997, Imbriano signed on as the Pats marketing director, and McDonough went with him. He also enrolled at BC, and started taking classes at the school of management. He worked for the Patriots two to three days a week, gaining experience in sales, community relations, and a host of other marketing subgenres.

When he graduated in 2002, McDonough was given a full-time job in the Patriots front office. Imbriano soon appointed McDonough a player liaison for his marketing group. Now anyone looking for a Patriot to show up at an event went through him. In his new position, McDonough had ample time to pal around with the team. He was roughly the same age as many of the players. He knew the city and liked to go out. But it was Brady, in particular, with whom he connected. The quarterback saw a kindred spirit in McDonough and began seeking him out for advice, not just about team issues, but about Boston, about life.

Was it at this point that McDonough started wearing suits in the locker room? Or driving a BMW 540i? (A Cadillac Escalade, Lexus SUV, and Range Rover would follow.) By 2004, an increasing amount of McDonough’s time was spent dealing with Brady, whose sisters were still handling much of his schedule. But the quarterback had started dating Moynahan. He was a two-time Super Bowl MVP etching his name into the NFL record books. His expanding celebrity demanded a professional-grade filter. McDonough—a friend, a Pats insider, not a sister—was the ideal guy for the job.

Sure enough, Brady’s “butler” was soon everywhere, behaving very little like a butler. People were confused about his position. Was he an agent? An assistant? A bunco man?

“He was always talking about making deals,” says McDonough’s friend Roy MacDowell III, a real estate developer with the firm Boulder Capital. There was McDonough partying with members of the team at Union Bar & Grille. There he was flying with Brady to Lindsay Lohan’s New Year’s bash. There he was shooting bull at Sonsie with new BC football coach Jeff Jagodzinski and Robert Withers, an executive at Marquis Jet, a private airline Brady uses. (Neither Jagodzinski nor Withers responded to interview requests.) The people at Sonsie say McDonough became such a regular at the swish establishment and entertained so many heavy hitters there that the owners decided to name a drink after him. It’s called the Will Thrill. Ingredients: Stoli orange vodka, Citrónge, and orange juice topped with sparkling wine.

If one moment stands out in McDonough’s upward scramble during this period, it occurred during a home game against the Jets on December 4, 2005. Gisele Bündchen was at Foxboro that day, handing out Victoria’s Secret prizes and steaming up the end-zone JumboTrons. McDonough knew her from a past promotional project and had surely noted what she’d told the Inside Track after seeing a photo of Brady: “definitely not too shabby.” Here was an opportunity for a very sweet deal.

About a year later, on January 14, 2007, mere weeks after Brady formally dumped a pregnant Moynahan, McDonough was spotted with Bündchen in the bowels of San Diego’s Qualcomm Stadium after the Patriots’ playoff win over the Chargers. Bündchen would later tell GQ that “a friend who knew us both” had fixed her up with Brady. A source close to Brady confirms it was McDonough. “Will would smuggle [Bündchen] in,” claims a friend of Brady’s. “Tom was on his way out with Bridget. He can’t see Gisele Bündchen without people noticing.” A different friend says Brady had ended things with Moynahan several months earlier. And that Brady hadn’t even been on an actual date with Bündchen when she was spotted outside the locker room in San Diego.

No matter. The paparazzi and gossip queens began foaming. In the press, the star athlete and the supermodel were an instant item. In the blogosphere, McDonough was a “pimp,” accused of abetting Brady’s supposed playboy lifestyle by planning dates with a bevy of women and keeping it quiet so Moynahan wouldn’t find out. Another view might be that he was simply doing his job—what better way for an aide-de-camp to demonstrate his value than to gift-wrap the world’s hottest supermodel? It was also a shrewd marketing move: Brady and Bündchen have become one of those megacouples whose conjoined fame is greater than the sum of its parts.

By last year McDonough had cemented his place in Brady’s retinue. He had moved into a Commonwealth Avenue penthouse a few doors down from the quarterback’s pad. He started showing up in photographs wearing designer outfits similar to Brady’s. He seemed to develop a Brady “mode” that was different from the laid-back persona his friends remember. People who have dealt with McDonough in a professional setting say he can sometimes be confident to the point of being cocky. On the field, that’s called swagger. Off the field, it’s attitude.

A magazine staffer who worked on a Brady photo shoot last year says McDonough stalked onto the set wearing a navy pinstripe suit and a BlackBerry on his belt and proceeded to behave like a discount David Falk. “He seemed like a cheesy L.A. agent,” the staffer says. “Any time Brady would come out in a different look, [McDonough] would be like, ‘Yeah, man, totally,’ or, ‘No, don’t wear that.’ It was never even clear what his role was or if we could tell him to butt out. He just seemed to have opinions on everything. It was escalating into diva-ish behavior.”

Brady said little during the photo shoot; McDonough did most of the talking. “[He] was a little bit drunk with his power,” the staffer says. “He really seemed like a kid in a suit with a lot of gumption.”

But then, maybe gumption is what’s called for. By this past February, the Brady brand that McDonough had helped build had grown
bigger than the Patriots front office could handle. It demanded a dedicated steward. McDonough decamped for New York, to plant his professional flag in the marketing big leagues. He’s now a VP of marketing at Avenue Capital, a $20 billion hedge fund. Chelsea Clinton works there. McDonough knows her, and her mom and dad. Avenue Capital is a place where the connections McDonough has cultivated will serve him well. He’s networking, raising money, making new kinds of deals. It’s the same hustle he honed working for WEEI and the Patriots, only with a lot more zeros attached. Some of those zeros come from Brady: The quarterback is an investor in the fund.

Along with the gig at Avenue, McDonough still represents Brady and is trying to make good as an independent manager of talent. He’s named his one-man management company CAVU, an aviation acronym for “ceiling and visibility unlimited.” His website, which features a backdrop of clouds and a bold line-art logo that would not be out of place in 1930s Germany, bills itself as the “portal through which powerful brands have been marrying powerful brands for years.” In his new venture, McDonough is said to have already helped Bündchen on a few projects.

As he looks for more clients, the question that will dog him, fairly or not, is whether he can be something more than Brady’s borrowed Rolodex. As if to answer those doubters, McDonough has been showing up sans Brady at soirees for the moneyed class. He skipped a Brady party on the Fourth of July on Beacon Street to watch fireworks with various movers and shakers in Aspen.

The previous month, he appeared without his famous patron at a Celtics dinner in Los Angeles during the NBA Finals. To get there, McDonough hitched a ride on the private jet of Jim Pallotta, a co-owner of the Celtics and the obscenely wealthy hedge fund manager for Tudor Investment Corporation. Another good guy to know.

At the Celtics dinner, which took place at Todd English’s joint Beso, the fact that McDonough was without Brady had some team insiders clucking. “Everyone was kind of joking about him,” one guest says. “Some of the people were saying, ‘Who the fuck is this guy? What kind of weird shit is going on?’ He shows up at all these big parties and walks around like the cat’s meow.”

Time and again in sports we find strange life forms affixed to the underbellies of athletes. Most are remoras clingy enough to shame limpets. They are the kind that sucked Mike Tyson dry, and ruined Johnny Unitas. McDonough isn’t like that. But that doesn’t stop people from wondering. “A lot of Tommy’s former teammates are pretty skeptical of Will,” says a friend. “We have other friends who have been railroaded into doing something with hustlers…. You always worry about guys that do well and have guys that hang around.”

Guys that hang around. Or always happen to be in the right place at the right time. Guys who trade their clout on Madison Avenue. Guys whose friends don’t really know them. It sounds weird, all right. But then again, being the greatest quarterback on the planet, taking trips to Ibiza, and waking up next to Gisele sounds pretty weird, too. Maybe Brady needs McDonough to normalize a world that none of us can truly fathom. Maybe.

We can only guess. What’s clear is that for now McDonough seems willing to endure the downside of the wraithlike presence he’s cultivated. He’s happy if Brady’s happy. And lately Brady has been happy. Last year he turned in arguably the greatest single-season performance ever for a quarterback. If he wins another Super Bowl, he’ll join Terry Bradshaw and boyhood idol Joe Montana as the only quarterbacks with four rings. The swagger will be impetuous. The brand will be unstoppable. McDonough will remain invisible.

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